JPS63159460A - Resin composition for lens - Google Patents
Resin composition for lensInfo
- Publication number
- JPS63159460A JPS63159460A JP61307540A JP30754086A JPS63159460A JP S63159460 A JPS63159460 A JP S63159460A JP 61307540 A JP61307540 A JP 61307540A JP 30754086 A JP30754086 A JP 30754086A JP S63159460 A JPS63159460 A JP S63159460A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- monomer
- 80pts
- resin composition
- formulas
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000011342 resin composition Substances 0.000 title claims description 8
- 239000000178 monomer Substances 0.000 claims abstract description 15
- 229920001577 copolymer Polymers 0.000 claims abstract description 4
- 239000000126 substance Substances 0.000 claims 6
- 229920005989 resin Polymers 0.000 abstract description 7
- 239000011347 resin Substances 0.000 abstract description 7
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract description 6
- 238000000465 moulding Methods 0.000 abstract description 5
- 239000000203 mixture Substances 0.000 abstract description 3
- BJELTSYBAHKXRW-UHFFFAOYSA-N 2,4,6-triallyloxy-1,3,5-triazine Chemical compound C=CCOC1=NC(OCC=C)=NC(OCC=C)=N1 BJELTSYBAHKXRW-UHFFFAOYSA-N 0.000 abstract description 2
- YMOONIIMQBGTDU-VOTSOKGWSA-N [(e)-2-bromoethenyl]benzene Chemical compound Br\C=C\C1=CC=CC=C1 YMOONIIMQBGTDU-VOTSOKGWSA-N 0.000 abstract description 2
- 230000005855 radiation Effects 0.000 abstract 2
- 230000000379 polymerizing effect Effects 0.000 abstract 1
- 239000011521 glass Substances 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 239000004793 Polystyrene Substances 0.000 description 3
- 238000001723 curing Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000004417 polycarbonate Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000003504 photosensitizing agent Substances 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 238000002834 transmittance Methods 0.000 description 2
- KMNCBSZOIQAUFX-UHFFFAOYSA-N 2-ethoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCC)C(=O)C1=CC=CC=C1 KMNCBSZOIQAUFX-UHFFFAOYSA-N 0.000 description 1
- BQZJOQXSCSZQPS-UHFFFAOYSA-N 2-methoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OC)C(=O)C1=CC=CC=C1 BQZJOQXSCSZQPS-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical group C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 description 1
- SYFOAKAXGNMQAX-UHFFFAOYSA-N bis(prop-2-enyl) carbonate;2-(2-hydroxyethoxy)ethanol Chemical compound OCCOCCO.C=CCOC(=O)OCC=C SYFOAKAXGNMQAX-UHFFFAOYSA-N 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 239000005038 ethylene vinyl acetate Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000000016 photochemical curing Methods 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 238000012719 thermal polymerization Methods 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 239000000326 ultraviolet stabilizing agent Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/30—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野〕
本発明は、レンズ材料、史に詳しく云えば辺明かつ間屈
折率を有する新規なレンズ用便ｎａ組放物に関する。DETAILED DESCRIPTION OF THE INVENTION (Field of Industrial Application) The present invention relates to a lens material, and more specifically to a novel lens paraboloid having a bright and intermediate refractive index.
（従来の技術）
従来、無機カラスに代わる台成柄脂については、稗々研
究さｒＬ提案さｎているが、欠点も多く、ｆだ実用の域
に達していない。？ｌＪ、ｔば、ジエチレングリコール
ビスアリルカーボネートを主成分とする重合物は、眼鏡
レンズ及びｙｔ、宇レンズとして実用化さ７しているが
、継計、安全性、加工容易性、染色性等の灯礪ガラスで
は７ｆ４たし得ない利点がある。しかしながら、この重
合物の屈折率は低く約１．５０″′Ｃあり、硬化方法が
熱重合である１こめ成形に長時間を要するという欠点が
ある。(Prior Art) In the past, extensive research has been carried out and proposals have been made regarding the use of molded resin to replace inorganic glass, but it has many drawbacks and has not yet reached the level of practical use. ? Polymers containing diethylene glycol bisallyl carbonate as the main component have been put into practical use as eyeglass lenses and lenses, but there are some issues with respect to suitability, safety, ease of processing, dyeability, etc. 7f4 has advantages that cannot be achieved with plain glass. However, the refractive index of this polymer is low, about 1.50''C, and the curing method is thermal polymerization, which is disadvantageous in that it takes a long time to mold.
一方、この欠点ケ改良した蘭屈廿丁率樹脂についても提
案さｎている。例えば、ポリカーボネート、ポリスチレ
ン糸の高屈折率樹脂があるが、熱Ｂ１塑性拉→脂である
ため、成形時に配回を生じ成るいは切削加工性、耐溶剤
性及び表面硬度に問題がある。On the other hand, a polyurethane resin that has improved this drawback has also been proposed. For example, there are high refractive index resins such as polycarbonate and polystyrene threads, but because they are thermal B1 plastic resins, they cause alignment during molding or have problems with machinability, solvent resistance, and surface hardness.
（発明が解決しようとする問題点）
以上、無機ガラスに代わる合成樹８ピとして解決すべき
問題点を工、透明性で高屈折率を有し、加工性が良く、
機械的性質が優ｎかつ成形サイクルが短いことという特
性を具えることである。(Problems to be solved by the invention) As described above, the problems to be solved as a synthetic resin 8-pole instead of inorganic glass are as follows: It has transparency, high refractive index, good workability,
It has the characteristics of excellent mechanical properties and a short molding cycle.
（問題点ｔｍ決するための手段）
本発明者等は、以上の問題点にかんがみ、鋭意研究の結
果前記の全特性を具えたレンズ用樹脂組成物を完成した
。(Means for Resolving the Problems) In view of the above problems, the present inventors conducted intensive research and completed a resin composition for lenses having all of the above characteristics.
ａち、本発明は、一般式中で表りさｎる１棟または２種
以上の第１単量体と、一般式（１１）で表わさｎる１ａ
または２棟以上の第２単量体と、こｎらとラジカル共重
酋司能な１槓または２種以上の第３単量体との共重合体
を主成分とする樹脂組成物である。a, the present invention provides one or more types of first monomers represented in the general formula, and 1a represented by the general formula (11);
Or, it is a resin composition mainly composed of a copolymer of two or more second monomers and one or more third monomers capable of radical copolymerization. .
次に、一般式中は、
ＣＨｚ＝Ｃ−Ｃ−ＯＲｓ ＜１）
′Ｃ，６つ、一般式（Ｉｔ）は
（式中、Ｒ＝Ｈ又ｉｓ ＣＨｓ、Ｘ＝ＣＨ，Ｃ）１，０
又ｔｓＣＨ鵞Ｃ）１０． ｍ ＋ ｎ ＝ ２ ” ３
０ ｔ”示す）占Ｈ３
である。第３率量体とじてを１、ラジカル重台可能な単
量体であｒｔは特に制限は無いが、尚７ｔＢ？ｒ率、高
アツベ数を得るためには、一般式（１１１）、及びＩＭ
で表わさｒＬる単量体や、スチレン、ブロモスチレン等
のスチレン−４体、トリアリルシアヌレート、トリアリ
ルイン７アヌレート寺のアリル化曾物などが好ましい。Next, in the general formula, CHz=C-C-ORs <1) 'C, 6, the general formula (It) is (in the formula, R=H or is CHs, X=CH, C) 1,0
Also tsCH Goose C) 10. m + n = 2 ” 3
The third polymer is 1, and there is no particular restriction on rt, which is a monomer capable of radical loading, but in order to obtain a 7tB?r rate and a high Atsube number. contains the general formula (111), and IM
Preferred are monomers represented by rL, 4-styrene units such as styrene and bromostyrene, allylated derivatives of triallyl cyanurate and triallyl-7-anurate, and the like.
（式中Ｒ＝Ｈ又はＣ市ン ＯＣＨ。(In the formula, R=H or C OCH.
（式中Ｒ＝Ｈ又はＣＨｓ ）
本発明の樹脂ｊｄｌｌ成物の硬化方法は、熱Ｘ曾及び紫
外触照射による１１Ｌ台ｔ−通用しうるが、成形サイク
ルを短縮するために蚤了紫外線照刺による重合が好まし
い。(In the formula, R=H or CHs) The curing method of the resin JDll composition of the present invention is applicable to 11L level using heat X and ultraviolet irradiation, but in order to shorten the molding cycle, ultraviolet irradiation is Polymerization by is preferred.
本発明の樹脂組成物には一般に知らＩしている光増感剤
、例えは、ジベンゾイル、ベンゾインメチルエーテル、
ベンゾインエチルエーテル、２−ヒドロ午シー２−ベン
ゾイルプロパン、２−ヒドロキシ−２−メチル−１−２
エニループａパン−１−オン、２，２−ジメトキ７−２
−フェニルアセトフェノン等を使用することがでさる。The resin composition of the present invention may contain commonly known photosensitizers such as dibenzoyl, benzoin methyl ether,
Benzoin ethyl ether, 2-hydro-2-benzoylpropane, 2-hydroxy-2-methyl-1-2
enilup a pan-1-one, 2,2-dimethoxy7-2
- Phenylacetophenone etc. can be used.
こｎらの光増感剤は、樹脂Ｉｆｉ成物に対して多くとも
５率量部の量で用すらｒＬる。又、不発明の樹脂組成物
には、本発明の効果ｔそこなわぬ範囲て公知の脩加剤、
ガえは、黄変防止剤、レベリング剤、紫外線吸収剤、紫
外〜安定剤、帯電防止剤、？化防止剤等を配せしても良
い。These photosensitizers may be used in amounts of at most 5 parts by weight based on the resin Ifi composition. In addition, the uninvented resin composition may contain known additives without detracting from the effects of the present invention.
Is it an anti-yellowing agent, a leveling agent, an ultraviolet absorber, an ultraviolet stabilizer, an antistatic agent, etc. An anti-oxidation agent or the like may be added.
実施例
本発明の実施例を次に説明する。用いた第１、第２、第
３率柑体は次の辿りである。Examples Examples of the present invention will be described below. The first, second, and third ratios used are as follows.
一般式中圧ついては
一般式＋１１７については
す
＋ＣＨａ ＣＨＤ、 ＣＣ＝ＣＨ２（以下りと略記する
）〇
一般式印については
〇
一般式ｔＮＪについては
を用い１こ。For pressure in the general formula, use +CHa for the general formula +117, CHD, CC=CH2 (abbreviated as below)〇For the general formula mark, use〇For the general formula tNJ, use 1 here.
直径１００１１１ｆｆｌのガラス叛とエチレン−酢酸ビ
ニル共重せ体からなるカスケラトで構成された鋳型を用
意し、この鋳型中に２重量部の１−（４−イングロビル
フェニル）−２−ヒドロキシ−２−メチルプロパン−１
−オンｆｔｍ’ＪＸＪ、ｍ酋した第１表Ｎ１〜陽６の各
種樹脂組成物を注入し、８０Ｗ／ＣＤ＋高圧水歓灯を用
いて胸囲から紫外線を照射した。６０秒間硬化し１こ恢
、ガスケート及びモールドからＭ合体をとり出した。A mold composed of a glass diaphragm with a diameter of 100111 ffl and a caskerato made of an ethylene-vinyl acetate copolymer was prepared, and 2 parts by weight of 1-(4-inglobylphenyl)-2-hydroxy-2- Methylpropane-1
Various resin compositions of Table 1 N1 to 6 were injected with ftm'JXJ and m, and ultraviolet rays were irradiated from around the chest using an 80W/CD + high-pressure water lamp. After curing for 60 seconds, the M combination was removed from the gasket and mold.
このようにして、得らｎた重合体の＃６＠性を測定して
第１表に示した。The #6 properties of the obtained polymers were measured and shown in Table 1.
第１表に示す諸物性の演り足は次の方法にＬった０
（１）屈折率（ｎに）
アツベの屈折計上用いて、２０℃における屈折５＄を測
定した。又、アツベ欽も甘わせて求めた。接＠液には、
七ノブロモナフタリンを使用した。The various physical properties shown in Table 1 were calculated using the following method. (1) Refractive index (n) Using an Atsube refractometer, the refraction at 20°C was measured at 5$. Also, Atsube Kin also asked for indulgence. For wetted liquid,
Seven-nobromonaphthalene was used.
（２） 光透過率（Ｔｔ％）
紫外分光元度計にて波長５８０ ｎｍの光透過′４を沖
Ｊ定した。(2) Light transmittance (Tt%) Light transmittance '4 at a wavelength of 580 nm was determined using an ultraviolet spectrometer.
（３１切削加工性
グラインダーにて切削し、ひび割ｒＬセずにきｎいに切
ｎるものを０１ひび割九巳ないが、切削した粉が若干残
査するものをΔ、ひび割ｎ又を工粉が強固に残査するも
のをＸで示した。(31 Machinability: 01: Cutting workability: 01: Cutting workability: 01: Cutting with a grinder without cracking; Those in which milled powder remained strongly are marked with an X.
第 １ 表
Ｓｔ スチレン
ＰＣポリカーボネート
ＰＳポリスチレン
以下余白
（発明の効果）
第１表忙示す測定数値によって明らかなよう和、本発明
の樹脂組成物を用いると、尚屈折率を有し、透明性が尚
（、切削加工性に優ｎたレンズが製造できると共に光硬
化によりＩＨ１時間で成形出来るので生産性が高くなる
効果がある。Table 1 St Styrene PC Polycarbonate PS Polystyrene Below Margin (Effects of the Invention) As is clear from the measured values shown in Table 1, when the resin composition of the present invention is used, it still has a refractive index and transparency. (This method has the effect of increasing productivity because lenses with excellent machinability can be manufactured and can be molded in 1 hour using IH by photocuring.)
ヶ、Ｊい、ツよよ、イ ベG, J, Tsuyo, Ibe
Claims (1)
式、表等があります▼、▲数式、化学式、表等がありま
す▼、又は▲数式、化学式、表等があります▼を示す） で表わされる第１単量体１０〜８０重量部と、一般式（
II） ▲数式、化学式、表等があります▼（II） （式中Ｒ＝Ｈ又はＣＨ＿３、Ｘ＝ＣＨ＿２ＣＨ＿２Ｏ又
は▲数式、化学式、表等があります▼、ｍ＋ｎ＝２〜３
０を示す） で表わされる第２単量体１０〜８０重量部とこれらとラ
ジカル共重合可能な第３単量体 １０〜８０重量部とからなる共重合体からなることを特
徴とするレンズ用樹脂組成物。[Claims] 1. General formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) (In the formula, R_1=H or CH_3, R_2=▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲Mathematical formulas , chemical formula, table, etc. ▼ or ▲ numerical formula, chemical formula, table, etc. ▼) 10 to 80 parts by weight of the first monomer represented by the general formula (
II) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(II) (In the formula, R=H or CH_3, X=CH_2CH_2O or ▲There are mathematical formulas, chemical formulas, tables, etc.▼, m+n=2~3
A copolymer comprising 10 to 80 parts by weight of a second monomer represented by 0) and 10 to 80 parts by weight of a third monomer radically copolymerizable with these monomers. Resin composition.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61307540A JPS63159460A (en) | 1986-12-23 | 1986-12-23 | Resin composition for lens |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61307540A JPS63159460A (en) | 1986-12-23 | 1986-12-23 | Resin composition for lens |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS63159460A true JPS63159460A (en) | 1988-07-02 |
Family
ID=17970322
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61307540A Pending JPS63159460A (en) | 1986-12-23 | 1986-12-23 | Resin composition for lens |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS63159460A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5384380A (en) * | 1993-01-14 | 1995-01-24 | Daiso Co., Ltd. | Polymerizable compositions and high refractive plastic lens obtained therefrom |
-
1986
- 1986-12-23 JP JP61307540A patent/JPS63159460A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5384380A (en) * | 1993-01-14 | 1995-01-24 | Daiso Co., Ltd. | Polymerizable compositions and high refractive plastic lens obtained therefrom |
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